Rye

Day Trips

Make the most of your day with our curated plans, packed with Rye's hidden gems and unique experiences!

day 1
Exploring the Historic Downtown
morning
:

Start your adventure with a leisurely breakfast at a quaint cafe in the historic downtown area. Afterward, wander through the charming streets, taking in the quaint architecture and vibrant local shops that showcase the town's history. Don’t forget to snap some photos in front of notable sites like the Rye Historical Society.

afternoon
:

After lunch at a local eatery, head over to the Rye Nature Center for a guided nature walk through the beautiful woodlands. Explore interactive exhibits that highlight the area’s rich biodiversity and enjoy the serenity of the surrounding environment. A visit to the center also offers opportunities to spot various wildlife native to the region.

evening
:

As the sun sets, enjoy dinner at a waterfront restaurant overlooking the Long Island Sound. Savor fresh seafood while relaxing in a cozy atmosphere and watching the boats glide by. Conclude your day with a stroll along the waterfront, soaking in the peaceful ambiance and ocean breezes.

day 2
Beach Day at Rye Town Park
morning
:

Begin your day early with a refreshing swim at Rye Town Park before the crowds arrive. Enjoy a light breakfast on the beach and take a moment to watch the sunrise over the water. The serenity of the morning will set a perfect tone for a fun-filled day ahead.

afternoon
:

Pack a picnic for lunch and find a shaded spot on the beach to enjoy your meal. Afterward, engage in some beach activities such as volleyball or paddleboarding, or simply relax on a towel with a good book. The vibrant atmosphere at the park will keep you entertained while basking in the sun.

evening
:

As evening approaches, join locals for an outdoor movie night in the park, if available. Grab some ice cream from a nearby vendor and settle in for a classic film under the stars. This unforgettable experience adds a communal touch to your beach day, creating lasting memories.

day 3
Day Trip to Manursing Island
morning
:

Catch a ferry over to Manursing Island for a unique island experience off the coast of Rye. Enjoy breakfast aboard the ferry as you take in stunning views of the water and skyline. Once on the island, start with a guided nature walk to learn about the local flora and fauna.

afternoon
:

Spend the afternoon swimming in the pristine waters or lounging on the sandy beaches of the island. Pack a lunch to enjoy in one of the picturesque picnic spots surrounded by nature. You could also explore the small hiking trails that offer panoramic views of the Sound.

evening
:

As the day winds down, hop back on the ferry and enjoy the sunset from the water, providing an unforgettable backdrop. After returning to Rye, treat yourself to dinner at a local bistro. Reflect on your day while enjoying delicious food and a cozy atmosphere.

day 4
Art and Culture Immersion
morning
:

Visit the Rye Arts Center after breakfast to explore local art exhibits, participate in workshops, or take a tour of the artistic space. The center regularly hosts classes and events that give insight into the local art scene. Immerse yourself in creativity and perhaps even make a small piece to take home.

afternoon
:

Afterward, grab lunch at a nearby café and continue your cultural exploration with a visit to the historic Jay Heritage Center. Take a guided tour to learn about the significant historical narratives that shaped the area. The gardens surrounding the center offer a peaceful space to relax and enjoy the scenery.

evening
:

In the evening, attend a local theater performance or live music event at one of Rye's cultural hotspots. Savor dinner at a nearby restaurant that highlights local gastronomy while sharing your experiences from the day with fellow attendees. Conclude the evening with casual conversations, inspired by the arts.

day 5
Outdoor Adventure at the Marshlands Conservancy
morning
:

Start your day with breakfast and then venture into the Marshlands Conservancy for an exciting morning of hiking and birdwatching. The serene landscape provides opportunities to connect with nature while observing a variety of wildlife. Breathe in the fresh air as you roam the well-marked trails.

afternoon
:

Enjoy a packed lunch at one of the scenic overlooks, admiring the beautiful marshlands and the wildlife they attract. Afterward, continue exploring the trails or participate in a guided nature program hosted by the conservancy. The afternoon is perfect for learning about conservation efforts in this vital ecosystem.

evening
:

As the daylight fades, return to your accommodations to relax before dinner. Consider dining at a restaurant featuring farm-to-table fare that showcases seasonal ingredients. Enjoy the ambiance as you reflect on the day's adventures in nature.

day 6
Wine Tasting in Nearby Hudson Valley
morning
:

Delight in a hearty breakfast before setting off on a day trip to the picturesque vineyards of Hudson Valley. The drive offers beautiful scenery, perfect for enjoying the autumn colors or spring blooms. Arrive at your first winery ready to explore the local winemaking process.

afternoon
:

Spend the afternoon visiting various vineyards, enjoying wine tastings paired with artisanal cheeses and local bites. Each winery provides a unique experience, complete with beautiful views and often scenic outdoor spaces. Engage with local wine experts and learn about the intricacies of winemaking in the Hudson Valley.

evening
:

Wrap up your wine adventure with a delicious dinner at a local vineyard restaurant, celebrating the flavors of Hudson Valley cuisine. Savor pairing wines with your meal, deepening your appreciation for local produce and viniculture. Return to Rye under the stars, reflecting on a day filled with exquisite food and drink.

day 7
Family Fun at Rye Playland
morning
:

Start the day with breakfast at a local diner before heading over to Rye Playland, a historic amusement park. Enjoy the thrill of rides suitable for all ages, creating joyful memories with your family. The ambiance of the park, adorned with classic architecture, sets an exciting tone as you arrive.

afternoon
:

Continue to enjoy the numerous rides and games scattered throughout the park. Have a leisurely lunch with picnic-style options to recharge for more adventures. Don’t miss the old-fashioned carousel and the waterfront views for some great photo opportunities.

evening
:

As dusk settles in, participate in the park's evening festivities, potentially including fireworks or themed events. Wind down with a casual dinner at a nearby eatery, reminiscing about the day's roller coasters and games. This evening concludes a delightful day filled with laughter and thrills.

day 8
Relaxation and Spa Day
morning
:

Enjoy a slow morning with coffee and pastries at a cozy café, savoring every moment of your relaxing day ahead. Afterward, head to a local spa for a morning of pampering treatments including massages and facials. Take time to unwind and rejuvenate your mind and body.

afternoon
:

Post-spa, enjoy a light lunch at a nearby health-conscious restaurant, focusing on fresh and nutritious options. Spend the afternoon browsing boutiques or indulging in light shopping at local artisan shops. The leisurely pace will allow you to appreciate the town’s charm without feeling rushed.

evening
:

As the sun sets, enjoy a tranquil dinner at a restaurant with outdoor seating, allowing you to enjoy the warm evening air. Toast to a day of relaxation and self-care while indulging in delectable dishes made from seasonal ingredients. Conclude your evening with a peaceful walk, soaking in the beauty of Rye at night.

day 9
Historical Landmarks Tour
morning
:

Kick off your day with breakfast at a local bakery, then embark on a tour of Rye’s rich historical sites. Visit landmarks such as the original home of John Jay and learn about his impact on American history. Each stop offers insights and stories that highlight Rye’s significance in early American life.

afternoon
:

After visiting landmarks, have lunch at a nearby pub that features historic charm alongside a varied menu. Continue your journey by visiting the Rye Historical Society for exhibitions showcasing unique artifacts and important presences in Rye’s history. Engage with historians or volunteers to deepen your understanding of the local past.

evening
:

Spend the evening at a historical reenactment or community event, allowing you to fully immerse yourself in the life of bygone eras. Dinner can be enjoyed at an establishment that emphasizes traditional recipes inspired by the region’s past. Reflect on the day's explorations and stories as you wind down back at your accommodations.

Discover Rye

Read more in our Rye 2025 Travel Guide.

Rye Travel Guide